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Xanomeline
IUPAC name	5-[4-(hexyloxy)- 1,2,5-thiadiazol- 3-yl]- 1-methyl- 1,2,3,6- tetrahydropyridine
Identifiers
CAS number	131986-45-3
PubChem	60809
MeSH	xanomeline
SMILES	CCCCCCOC1=NSN=C1C2=CCCN(C2)C
Properties
Molecular formula	C14H23N3OS
Molar mass	281.42 g mol−1
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

Xanomeline is a muscarinic agonist with reasonable selectivity for the M1 and M4 subtypes.^[1]^[2]^[3]^[4] It has been studied for the treatment of both Alzheimer's disease and schizophrenia, particularly the cognitive and negative symptoms,^[5] although gastrointestinal side effects led to a high drop-out rate in clinical trials.^[6]^[7] Despite this, xanomeline has been shown to have reasonable efficacy for the treatment of schizophrenia symptoms, and one recent human study found robust improvements in verbal learning and short-term memory associated with xanomeline treatment.^[8]

[edit] References

^ Farde L, Suhara T, Halldin C, et al. (1996). "PET study of the M1-agonists [11C]xanomeline and [11C]butylthio-TZTP in monkey and man". Dementia 7 (4): 187–95. PMID 8835881.
^ Jakubík J, Michal P, Machová E, Dolezal V (2008). "Importance and prospects for design of selective muscarinic agonists". Physiol Res 57 Suppl 3: S39–47. PMID 18481916. http://www.biomed.cas.cz/physiolres/pdf/57%20Suppl%203/57_S39.pdf.
^ Woolley ML, Carter HJ, Gartlon JE, Watson JM, Dawson LA (January 2009). "Attenuation of amphetamine-induced activity by the non-selective muscarinic receptor agonist, xanomeline, is absent in muscarinic M4 receptor knockout mice and attenuated in muscarinic M1 receptor knockout mice". Eur. J. Pharmacol. 603 (1-3): 147–9. doi:10.1016/j.ejphar.2008.12.020. PMID 19111716.
^ Heinrich JN, Butera JA, Carrick T, Kramer A, Kowal D, Lock T, Marquis KL, Pausch MH, Popiolek M, Sun SC, Tseng E, Uveges AJ, Mayer SC (March 2009). "Pharmacological comparison of muscarinic ligands: historical versus more recent muscarinic M1-preferring receptor agonists". Eur. J. Pharmacol. 605 (1-3): 53–6. doi:10.1016/j.ejphar.2008.12.044. PMID 19168056.
^ Lieberman JA, Javitch JA, Moore H (August 2008). "Cholinergic agonists as novel treatments for schizophrenia: the promise of rational drug development for psychiatry". Am J Psychiatry 165 (8): 931–6. doi:10.1176/appi.ajp.2008.08050769. PMID 18676593.
^ Messer WS (2002). "The utility of muscarinic agonists in the treatment of Alzheimer's disease". J. Mol. Neurosci. 19 (1-2): 187–93. doi:10.1007/s12031-002-0031-5. PMID 12212779.
^ Mirza NR, Peters D, Sparks RG (2003). "Xanomeline and the antipsychotic potential of muscarinic receptor subtype selective agonists". CNS Drug Rev 9 (2): 159–86. PMID 12847557.
^ Shekhar A, Potter WZ, Lightfoot J, Lienemann J, Dubé S, Mallinckrodt C, Bymaster FP, McKinzie DL, Felder CC (August 2008). "Selective muscarinic receptor agonist xanomeline as a novel treatment approach for schizophrenia". Am J Psychiatry 165 (8): 1033–9. doi:10.1176/appi.ajp.2008.06091591. PMID 18593778.

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[pmid8835881-0] Farde L, Suhara T, Halldin C, et al. (1996). "PET study of the M1-agonists [11C]xanomeline and [11C]butylthio-TZTP in monkey and man". Dementia 7 (4): 187–95. PMID 8835881.

[pmid18481916-1] Jakubík J, Michal P, Machová E, Dolezal V (2008). "Importance and prospects for design of selective muscarinic agonists". Physiol Res 57 Suppl 3: S39–47. PMID 18481916. http://www.biomed.cas.cz/physiolres/pdf/57%20Suppl%203/57_S39.pdf.

[pmid19111716-2] Woolley ML, Carter HJ, Gartlon JE, Watson JM, Dawson LA (January 2009). "Attenuation of amphetamine-induced activity by the non-selective muscarinic receptor agonist, xanomeline, is absent in muscarinic M4 receptor knockout mice and attenuated in muscarinic M1 receptor knockout mice". Eur. J. Pharmacol. 603 (1-3): 147–9. doi:10.1016/j.ejphar.2008.12.020. PMID 19111716.

[pmid19168056-3] Heinrich JN, Butera JA, Carrick T, Kramer A, Kowal D, Lock T, Marquis KL, Pausch MH, Popiolek M, Sun SC, Tseng E, Uveges AJ, Mayer SC (March 2009). "Pharmacological comparison of muscarinic ligands: historical versus more recent muscarinic M1-preferring receptor agonists". Eur. J. Pharmacol. 605 (1-3): 53–6. doi:10.1016/j.ejphar.2008.12.044. PMID 19168056.

[pmid18676593-4] Lieberman JA, Javitch JA, Moore H (August 2008). "Cholinergic agonists as novel treatments for schizophrenia: the promise of rational drug development for psychiatry". Am J Psychiatry 165 (8): 931–6. doi:10.1176/appi.ajp.2008.08050769. PMID 18676593.

[pmid12212779-5] Messer WS (2002). "The utility of muscarinic agonists in the treatment of Alzheimer's disease". J. Mol. Neurosci. 19 (1-2): 187–93. doi:10.1007/s12031-002-0031-5. PMID 12212779.

[pmid12847557-6] Mirza NR, Peters D, Sparks RG (2003). "Xanomeline and the antipsychotic potential of muscarinic receptor subtype selective agonists". CNS Drug Rev 9 (2): 159–86. PMID 12847557.

[shekhar-7] Shekhar A, Potter WZ, Lightfoot J, Lienemann J, Dubé S, Mallinckrodt C, Bymaster FP, McKinzie DL, Felder CC (August 2008). "Selective muscarinic receptor agonist xanomeline as a novel treatment approach for schizophrenia". Am J Psychiatry 165 (8): 1033–9. doi:10.1176/appi.ajp.2008.06091591. PMID 18593778.

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